Phosphorus oxychloride → HCID 57551813, compound

HRID 907292Notes

Reaction equation

HRID 907292 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:23]3[CH:24]=[C:25]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:26]([NH:28][CH:29]3[CH2:31][CH2:30]3)=[O:27])[CH:19]=2)[C:14]1=[O:36])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.BrC1C=C2C(=CC=1)[C:44](=[O:48])NC=C2>CN(C=O)C>[CH2:6]([N:13]1[CH:22]=[C:21]([CH:44]=[O:48])[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:23]3[CH:24]=[C:25]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:26]([NH:28][CH:29]3[CH2:31][CH2:30]3)=[O:27])[CH:19]=2)[C:14]1=[O:36])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 158851826-Bromoisoquinolin-1(2H)-oneHCID 25020345HCID 25020345, compound

Product 1

HCID 57551813HCID 57551813, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

DMF (5 mL) was cooled in an ice bath and phosphorus oxychloride (0.11 mL) added. The solution was stirred for 10 minutes. 3-(2-Benzyl-1-oxo-1,2-dihydroisoquinolin-6-yl)-N-cyclopropyl-4-methylbenzamide, Example 1 (0.4 g) was then added in one portion and the mixture heated at 80° C. for 6 hours. The mixture was allowed to cool then poured onto ice and stirred for 10 minutes. This was then extracted with ethyl acetate. The organics were combined and evaporated under reduced pressure. The residue was purified (SiO2, 1:1 isohexane/ethyl acetate) to give the sub titled compound (0.15 g).

Workup

  1. temperatureto cool
  2. additionthen poured onto ice
  3. stirringstirred for 10 minutes
  4. extractionThis was then extracted with ethyl acetate
  5. customevaporated under reduced pressure
  6. customThe residue was purified (SiO2, 1:1 isohexane/ethyl acetate)

Sources & evidence

ORD record
ord-4b08b6426c67430b9afaa16065a45c2e
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

Loading…